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[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

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Synonym(s):
Pd(dppf)Cl2
Linear Formula:
(C17H14P)2Fe · PdCl2
CAS Number:
Molecular Weight:
731.70
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

reaction suitability

core: palladium
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Buchwald-Hartwig Cross Coupling Reaction

mp

266-283 °C (lit.)

SMILES string

[Fe].Cl[Pd]Cl.[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6

InChI

1S/2C17H14P.2ClH.Fe.Pd/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;;;;/h2*1-14H;2*1H;;/q;;;;;+2/p-2

InChI key

JCWIWBWXCVGEAN-UHFFFAOYSA-L

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This Item
379670678740702005
reaction suitability

core: palladium, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Cross Couplings

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

mp

266-283 °C (lit.)

mp

275-280 °C

mp

-

mp

282-287 °C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

Application

Catalyst for C-C and C-N coupling reaction.
Pd(dppf)Cl2 may be used as an effective palladium catalyst in the following reactions:
  • Cross-coupling of sec-alkyl and n-alkyl Grignard reagents with high yield and selectivity.
  • Suzuki coupling of aryl boronic esters with [11C]methyl iodide to form functionalized [11C]toluene derivatives.
  • Kumada cross-coupling of 1,3,5-tribromobenzene with Grignard reagents to form star-shaped oligothiophenes.
For small scale and high throughput uses, product is also available as ChemBeads (919780)

related product

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Shirbin, S. J. et al.
Tetrahedron Letters, 51, 2971-2971 (2010)
Star?Shaped Oligothiophenes for Solution?Processible Organic Field?Effect Transistors.
Ponomarenko S
Advances in Functional Materials, 13(8), 591-596 (2003)
An improved synthesis of substituted [11C] toluenes via Suzuki coupling with [11C] methyl iodide
Hostetler E
Journal of Labelled Compounds & Radiopharmaceuticals, 48(9), 629-634 (2005)
Electrophilic activation of benzaldehydes through ortho palladation: one-pot synthesis of 3-methylene-indan-1-ols through a domino allylstannylation/Heck reaction under neutral conditions.
Ján Cvengros et al.
Angewandte Chemie (International ed. in English), 48(33), 6148-6151 (2009-07-11)
Shunsuke Chiba et al.
Journal of the American Chemical Society, 131(36), 12886-12887 (2009-08-25)
A Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via an unprecedented C-C bond cleavage-C-N bond formation sequence, providing substituted azaheterocycles.

Articles

Tandem hydroboration Suzuki Coupling both intermolecular and intramolecular gave diverse alkyl substituted products dppf

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